CN112390740A - Organic electroluminescent material and device - Google Patents
Organic electroluminescent material and device Download PDFInfo
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- CN112390740A CN112390740A CN202011376587.8A CN202011376587A CN112390740A CN 112390740 A CN112390740 A CN 112390740A CN 202011376587 A CN202011376587 A CN 202011376587A CN 112390740 A CN112390740 A CN 112390740A
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- alkyl
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- 239000000463 material Substances 0.000 title claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 111
- 239000010410 layer Substances 0.000 claims description 89
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 49
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 48
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 48
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 48
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 48
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 46
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 46
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 46
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 45
- 150000002825 nitriles Chemical class 0.000 claims description 41
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 40
- 229910052805 deuterium Inorganic materials 0.000 claims description 40
- 235000010290 biphenyl Nutrition 0.000 claims description 39
- 150000002527 isonitriles Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 239000004305 biphenyl Substances 0.000 claims description 37
- 239000003446 ligand Substances 0.000 claims description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 29
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 25
- 229930192474 thiophene Natural products 0.000 claims description 24
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 23
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 23
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 21
- -1 amino, silyl Chemical group 0.000 claims description 21
- 230000004888 barrier function Effects 0.000 claims description 21
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 21
- 125000005110 aryl thio group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000005580 triphenylene group Chemical group 0.000 claims description 13
- 229960005544 indolocarbazole Drugs 0.000 claims description 12
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 11
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 11
- LDEUQESGCXQVJF-UHFFFAOYSA-N 12H-[1]benzoselenolo[3,2-a]carbazole Chemical compound [se]1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 LDEUQESGCXQVJF-UHFFFAOYSA-N 0.000 claims description 10
- DERKMBVPWKXOHM-UHFFFAOYSA-N 12h-[1]benzofuro[3,2-a]carbazole Chemical compound O1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 DERKMBVPWKXOHM-UHFFFAOYSA-N 0.000 claims description 10
- GLYYLMBVQZMMMS-UHFFFAOYSA-N 12h-[1]benzothiolo[3,2-a]carbazole Chemical compound S1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 GLYYLMBVQZMMMS-UHFFFAOYSA-N 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 10
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 7
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 7
- 150000001716 carbazoles Chemical class 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 description 28
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000032258 transport Effects 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 125000004149 thio group Chemical group *S* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- NEVSKDGWKUIONI-UHFFFAOYSA-N 2-bromo-9-(3-triphenylen-2-ylphenyl)carbazole Chemical compound BrC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=CC(=CC=C1)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1 NEVSKDGWKUIONI-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- 150000001251 acridines Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 150000008316 benzisoxazoles Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001854 cinnolines Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002473 indoazoles Chemical class 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000005054 naphthyridines Chemical class 0.000 description 2
- 150000005063 oxadiazines Chemical class 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical class O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 150000002988 phenazines Chemical class 0.000 description 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 150000003195 pteridines Chemical class 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 150000003246 quinazolines Chemical class 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 150000003252 quinoxalines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Images
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Abstract
The present invention relates to organic electroluminescent materials and devices. The organic electroluminescent materials and devices comprise novel organic compounds containing oligomeric carbazoles. The compounds are suitable for use in organic light emitting diodes. The compounds are also suitable for use as charge transport and charge blocking layers, and as hosts in the light-emitting layer of an organic light-emitting device, OLED.
Description
This application is a divisional application of the invention patent application entitled "organic electroluminescent materials and devices" filed on application date 2015, 2/13, application number 201510078722.3.
The claimed invention is made by one or more of the following parties to a joint university company research agreement, in the name of and/or in conjunction with one or more of the following parties: the board of Michigan university, Princeton university, southern California university, and the world Display Corporation (Universal Display Corporation). The agreement is in effect on and before the date the claimed invention was made, and the claimed invention is made as a result of activities performed within the scope of the agreement.
Technical Field
The present invention relates to novel organic compounds containing oligomeric carbazoles. The compounds are suitable for use in organic light emitting diodes. The compounds are also suitable for use as charge transport and charge blocking layers, and as hosts in the light emitting layer of Organic Light Emitting Devices (OLEDs).
Background
Optoelectronic devices utilizing organic materials are becoming increasingly popular for several reasons. Many of the materials used to make such devices are relatively inexpensive, and therefore organic optoelectronic devices have the potential to gain cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them well suited for specific applications, such as fabrication on flexible substrates. Examples of organic optical electronic devices include Organic Light Emitting Devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials. For example, the wavelength of light emitted by the organic emissive layer can generally be readily tuned with appropriate dopants.
OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly attractive technology for use in, for example, flat panel displays, lighting, and backlighting applications. Several OLED materials and configurations are described in U.S. patent nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
One application of phosphorescent emissive molecules is full color displays. Industry standards for such displays require pixels adapted to emit a particular color (referred to as a "saturated" color). In particular, these standards require saturated red, green and blue pixels. Color can be measured using CIE coordinates well known in the art.
An example of a green emissive molecule is tris (2-phenylpyridine) iridium, denoted Ir (ppy)3It has the following structure:
in this and later figures herein, the dative bond from nitrogen to metal (here, Ir) is depicted as a straight line.
As used herein, the term "organic" includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. In some cases, the small molecule may include a repeat unit. For example, the use of long chain alkyl groups as substituents does not remove the molecule from the "small molecule" class. Small molecules can also be incorporated into polymers, for example as a pendant group on the polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the OLED art are small molecules.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed" on a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
As used herein, and as will be generally understood by those skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since Ionization Potential (IP) is measured as negative energy relative to vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (IP that is less negative). Similarly, a higher LUMO energy level corresponds to an Electron Affinity (EA) having a smaller absolute value (EA that is less negative). On a conventional energy level diagram, the vacuum level is at the top and the LUMO level of a material is higher than the HOMO level of the same material. The "higher" HOMO or LUMO energy level appears closer to the top of this figure than the "lower" HOMO or LUMO energy level.
As used herein, and as will be generally understood by those skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Since work function is typically measured as negative relative to vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram, the vacuum level is at the top, illustrating the "higher" work function as being farther from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
Further details regarding OLEDs and the definitions described above may be found in U.S. patent No. 7,279,704, which is incorporated herein by reference in its entirety.
Disclosure of Invention
A new class of compounds containing oligomeric carbazoles is provided.
The present invention provides compounds having formula I:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4、R5、R6、R7、R8、RAand RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2, or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, R1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBIs hydrogen.
In some embodiments, the compound is selected from the group consisting of: formula IV:
in some embodiments, G1The method comprises the following steps:
in some embodiments, G1Selected from the group consisting of:
in some embodiments, L is selected from the group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl;
wherein each is independently represented by the formula1、G2Or G3And one of them- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -1A direct bond of (2).
In some embodiments, G2The method comprises the following steps:
in some embodiments, G2Selected from the group consisting of:
in some embodiments, G3Selected from the group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl.
In some embodiments, the compound is selected from the group consisting of: compound 1 to compound 67.
In some embodiments, m is 1, L is benzene, and R is3、R4And RAIs hydrogen.
In some embodiments, m is 1, L is biphenyl, and R is3、R4And RAIs hydrogen.
In some embodiments, a first apparatus is provided. The first device comprises an anode; a cathode; and an organic layer disposed between the anode and the cathode comprising a compound having formula I:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
wherein R is1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroarylAryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, the organic layer is an emissive layer and the compound of formula I is a host.
In some embodiments, the organic layer further comprises a phosphorescent emissive dopant.
In some embodiments, the phosphorescent emissive dopant is a transition metal complex having at least one ligand or a portion of the ligand when the ligand is bidentate or more, the ligand selected from the group consisting of:
wherein R isa、Rb、RcAnd RdMay represent a mono-, di-, tri-or tetra-substituent or no substituent; and is
Wherein R isa、Rb、RcAnd RdIndependently selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein Ra、Rb、RcAnd RdTwo adjacent substituents in (a) are optionally linked to form a fused ring or to form a multidentate ligand.
In some embodiments, the organic layer is a barrier layer and the compound is a barrier material in the organic layer.
In some embodiments, the device is an organic light emitting device.
In some embodiments, the device comprises a compound selected from the group consisting of:
the present invention also provides a formulation comprising a compound having formula I:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4、R5、R6、R7、R8、RAand RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
Drawings
Fig. 1 shows an organic light emitting device.
Fig. 2 shows an inverted organic light-emitting device without a separate electron-transporting layer.
Figure 3 shows a compound of formula IV.
Figure 4 shows compounds of formula V.
Detailed Description
Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and a hole are confined to the same molecule, an "exciton," which is a localized electron-hole pair with an excited energy state, is formed. When the exciton relaxes via a photoemissive mechanism, light is emitted. In some cases, excitons may be confined to an excimer or exciplex. Non-radiative mechanisms (e.g., thermal relaxation) may also occur, but are generally considered undesirable.
The initial OLEDs used emissive molecules that emit light from a singlet state ("fluorescence"), as disclosed, for example, in U.S. patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a time frame of less than 10 nanoseconds.
More recently, OLEDs having emissive materials that emit light from the triplet state ("phosphorescence") have been demonstrated. Baldo (Baldo) et al, "Efficient Phosphorescent Emission from Organic Electroluminescent Devices" (Nature), 395 th volume, 151 th page 154, 1998; ("Baldolo-I") and Bardolo et al, "Very efficient Green organic light-emitting devices based on electro-phosphorescence" (Very high-efficiency green organic light-emitting devices), applied Physics (appl. Phys. Lett.), Vol.75, No. 3, pp.4-6 (1999) ("Baldolo-II"), which are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, columns 5-6, which is incorporated by reference.
Fig. 1 shows an organic light emitting device 100. The figures are not necessarily to scale. Device 100 may include substrate 110, anode 115, hole injection layer 120, hole transport layer 125, electron blocking layer 130, emissive layer 135, hole blocking layer 140, electron transport layer 145, electron injection layer 150, protective layer 155, cathode 160, and barrier layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of these various layers, as well as the example materials, are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704, which is incorporated by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive materials and host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
Fig. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. The device 200 may be fabricated by sequentially depositing the described layers. Because the most common OLED configuration has a cathode disposed over an anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 may be used. Fig. 2 provides one example of how some layers may be omitted from the structure of device 100.
The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be realized by combining the described individual layers in different ways, or several layers may be omitted entirely, based on design, performance and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it is understood that combinations of materials (e.g., mixtures of host and dopant) or, more generally, mixtures may be used. Also, the layer may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to fig. 1 and 2.
Structures and materials not specifically described, such as oleds (pleds) comprising polymeric materials, may also be used, such as disclosed in U.S. patent No. 5,247,190 to Friend et al, which is incorporated by reference in its entirety. As another example, an OLED having a single organic layer may be used. The OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest (Forrest) et al, which is incorporated by reference in its entirety. The OLED structure can deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling (out-coupling), such as a mesa structure as described in U.S. patent No. 6,091,195 to forrest et al, and/or a pit structure as described in U.S. patent No. 5,834,893 to Bulovic et al, which are incorporated by reference in their entirety.
Any of the layers of the various embodiments may be deposited by any suitable method, unless otherwise specified. For organic layers, preferred methods include thermal evaporation, ink jetting (e.g., as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, both incorporated by reference in their entirety), organic vapor deposition (OVPD) (e.g., as described in U.S. Pat. No. 6,337,102 to Foster et al, both incorporated by reference in their entirety), and deposition by Organic Vapor Jet Printing (OVJP) (e.g., as described in U.S. Pat. No. 7,431,968, incorporated by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. The solution-based process is preferably carried out in a nitrogen or inert atmosphere. For other layers, a preferred method includes thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (such as described in U.S. patent nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety), and patterning associated with some of the deposition methods, such as inkjet and OVJD. Other methods may also be used. The material to be deposited may be modified to be compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3 to 20 carbons are a preferred range. A material with an asymmetric structure may have better solution processibility than a material with a symmetric structure, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
Devices fabricated according to embodiments of the present invention may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapor, and/or gases, among others. The barrier layer may be deposited on, under or beside the substrate, electrode, or on any other part of the device, including the edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic compounds or organic compounds or both. Preferred barrier layers comprise a mixture of polymeric and non-polymeric materials as described in U.S. patent No. 7,968,146, PCT patent application nos. PCT/US2007/023098 and PCT/US2009/042829, which are incorporated herein by reference in their entirety. To be considered a "mixture," the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric material to non-polymeric material may be in the range of 95:5 to 5: 95. The polymeric material and the non-polymeric material may be produced from the same precursor material. In one example, the mixture of polymeric material and non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
Devices made according to embodiments of the present invention can be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and/or signaling, heads-up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, Personal Digital Assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, large area walls, theater or stadium screens, or signs. Various control mechanisms may be used to control devices made in accordance with the present invention, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18 degrees celsius to 30 degrees celsius, and more preferably at room temperature (20-25 degrees celsius), but may be used outside this temperature range (e.g., -40 degrees celsius to +80 degrees celsius).
The materials and structures described herein may be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.
As used herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine, and iodine.
As used herein, the term "alkyl" encompasses both straight-chain and branched-chain alkyl groups. Preferred alkyl groups are those containing one to fifteen carbon atoms and include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. In addition, the alkyl group may be optionally substituted.
As used herein, the term "cycloalkyl" encompasses cyclic alkyl groups. Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, and the like. In addition, cycloalkyl groups may be optionally substituted.
As used herein, the term "alkenyl" encompasses straight and branched chain alkenyl groups. Preferred alkenyl groups are those containing from two to fifteen carbon atoms. In addition, the alkenyl group may be optionally substituted.
As used herein, the term "alkynyl" encompasses straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing from two to fifteen carbon atoms. In addition, the alkynyl group may be optionally substituted.
As used herein, the terms "aralkyl" or "arylalkyl" are used interchangeably and encompass alkyl groups having an aromatic group as a substituent. In addition, the aralkyl group may be optionally substituted.
As used herein, the term "heterocyclyl" encompasses non-aromatic cyclic groups. Preferred heterocyclic groups are those containing 3 or 7 ring atoms including at least one heteroatom and include cyclic amines such as morpholinyl, piperidinyl, pyrrolidinyl and the like, and cyclic ethers such as tetrahydrofuran, tetrahydropyran and the like. In addition, the heterocyclic group may be optionally substituted.
As used herein, the term "aryl" or "aromatic group" encompasses monocyclic groups and polycyclic ring systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, the aryl group may be optionally substituted.
As used herein, the term "heteroaryl" encompasses monocyclic heteroaromatic groups that may include one to three heteroatoms, such as pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, pyrimidine and the like. The term heteroaryl also includes polycyclic heteroaromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles and/or heteroaryls. In addition, heteroaryl groups may be optionally substituted.
The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl groups may be optionally substituted with one or more substituents selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
As used herein, "substituted" means that a substituent other than H is bonded to the relevant position, e.g., carbon. Thus, for example, at R1When mono-substituted, then an R1Must not be H. Similarly, at R1When disubstituted, then two R1Must not be H. Similarly, at R1When unsubstituted, R1Hydrogen for all available locations.
The "aza" designation in a fragment described herein (e.g., aza-dibenzofuran, aza-dibenzothiophene, etc.) means that one or more C-H groups in the corresponding fragment can be replaced by a nitrogen atom, e.g., and without any limitation, azatriphenylene encompasses dibenzo [ f, H ] quinoxaline and dibenzo [ f, H ] quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.
It is understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it were a fragment (e.g., naphthyl, dibenzofuranyl) or as if it were the entire molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or connecting fragments are considered to be equivalent.
Various carbazole-containing compounds have been developed as organic electroluminescent materials. Depending on the unique way of building block linkages, these compounds have different energy levels, molecular packing and charge transport properties, all of which greatly affect device performance. The present invention discloses a new class of oligomeric carbazole compounds in which the carbazole moieties are attached at the 2-and 7-positions. Surprisingly, phosphorescent OLED devices using the compounds of the present invention as host materials exhibit superior performance compared to the compounds reported in the literature.
In some embodiments, compounds having formula I are provided:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene,Xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenothiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4、R5、R6、R7、R8、RAand RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2, or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, R1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBIs hydrogen.
In some embodiments, G1The method comprises the following steps:
in some embodiments, G1Selected from the group consisting of:
in some embodiments, L is selected from the group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl;
wherein each is independently represented by the formula1、G2Or G3And one of them- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -1A direct bond of (2).
In some embodiments, G2The method comprises the following steps:
in some embodiments, G2Selected from the group consisting of:
in some embodiments, G3Is selected from the group consisting ofThe group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl.
In some embodiments, the compound is selected from the group consisting of:
in some embodiments, m is 1, L is benzene, and R is3、R4And RAIs hydrogen.
In some embodiments, m is 1, L is biphenyl, and R is3、R4And RAIs hydrogen.
In some embodiments, compounds having formula IV are provided:
in the compound having formula IV, L is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4、R5、R6、R7、R8、RAand RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, compounds having formula V are provided:
in the compound having formula V, L is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2and R4Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1and R3Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4and RAEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof; and is
m is an integer of 1 to 10.
In some embodiments, a first apparatus is provided. The first device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, including a compound having formula I:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
wherein R is1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, the first device comprises a compound of formula IV. In some embodiments, the first device comprises a compound of formula V.
In some embodiments, the organic layer is an emissive layer and the compound of formula I is a host. In some embodiments, the organic layer is an emissive layer and the compound of formula IV is a host. In some embodiments, the organic layer is an emissive layer and the compound of formula V is a host.
In some embodiments, the organic layer further comprises a phosphorescent emissive dopant.
In some embodiments, the phosphorescent emissive dopant is a transition metal complex having at least one ligand or a portion of the ligand when the ligand is bidentate or more, the ligand selected from the group consisting of:
wherein R isa、Rb、RcAnd RdMay represent a mono-, di-, tri-or tetra-substituent or no substituent; and is
Wherein R isa、Rb、RcAnd RdIndependently selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein Ra、Rb、RcAnd RdTwo adjacent substituents in (a) are optionally linked to form a fused ring or to form a multidentate ligand.
In some embodiments, the organic layer is a barrier layer and the compound is a barrier material in the organic layer.
In some embodiments, the first device is a consumer product.
In some embodiments, the device is an organic light emitting device.
In some embodiments, the device includes a lighting panel.
In some embodiments, the device comprises a compound selected from the group consisting of:
in some embodiments, the compounds described herein are provided in a formulation with other materials present in the device. For example, the compounds of the present invention may be provided in formulations in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, or other layers.
In some embodiments, a formulation is provided comprising a compound having formula I:
in the compounds of the formula I, G1Having the formula II:
G2having formula III:
l is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
G3selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
R2、R4、R6and R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
R1、R3、R5and R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
R1、R2、R3、R4、R5、R6、R7、R8、RAand RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
l is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
G3optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
m is greater than n.
In some embodiments, the formulation comprises a compound of formula IV. In some embodiments, the formulation comprises a compound of formula V.
In combination with other materials
Materials described herein as useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. The materials described or referenced below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that can be used in combination.
HIL/HTL：
The hole injecting/transporting material used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as the hole injecting/transporting material. Examples of such materials include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivativesAn organism; indolocarbazole derivatives; a fluorocarbon-containing polymer; a polymer having a conductive dopant; conductive polymers such as PEDOT/PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; metal oxide derivatives, e.g. MoOx(ii) a p-type semiconductor organic compounds such as 1,4,5,8,9, 12-hexaazatriphenylhexacyano nitrile; a metal complex, and a crosslinkable compound.
Examples of aromatic amine derivatives used in the HIL or HTL include (but are not limited to) the following general structures:
Ar1to Ar9Each of which is selected from the group consisting of aromatic hydrocarbon ring compounds such as benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; from the group of aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazines, oxadiazines, indoles, benzimidazoles, indazoles, indoxazines, benzoxazoles, benzisoxazoles, benzothiazoles, quinolines, isoquinolines, cinnolines, quinazolines, quinoxalines, naphthyridines, phthalazines, pteridines, dibenzopyrans, acridines, phenazines, phenothiazines, phenoxazines, benzofuropyridines, furobipyridines, benzothienopyridines, thienobipyridines, benzoselenenopyridines, and selenophenodipyridines; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from an aromatic hydrocarbon ring group and an aromatic heterocyclic group, and are directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring groupAre bonded to each other. Wherein each Ar is further substituted with a substituent selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, Ar1To Ar9Independently selected from the group consisting of:
k is an integer from 1 to 20; x101To X108Is C (including CH) or N; z101Is NAr1O or S; ar (Ar)1Having the same groups as defined above.
Examples of metal complexes used in HILs or HTLs include, but are not limited to, the following general formulas:
met is a metal; (Y)101-Y102) Is a bidentate ligand, Y101And Y102Independently selected from C, N, O, P and S; l is101Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k' + k "is the maximum number of ligands that can be attached to the metal.
In one aspect, (Y)101-Y102) Is a 2-phenylpyridine derivative.
In another aspect, (Y)101-Y102) Are carbene ligands.
In another aspect, Met is selected from Ir, Pt, Os and Zn.
In another aspect, the metal complex has a relative Fc of less than about 0.6V+Solution minimum oxidation potential of the/Fc pair.
A main body:
the light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is larger than that of the dopant. Although the following table classifies the host materials that are preferred for devices emitting various colors, any host material may be used with any dopant as long as the triplet criteria are met.
Examples of the metal complex used as the host preferably have the following general formula:
met is a metal; (Y)103-Y104) Is a bidentate ligand, Y103And Y104Independently selected from C, N, O, P and S; l is101Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k' + k "is the maximum number of ligands that can be attached to the metal.
In one aspect, the metal complex is:
(O-N) is a bidentate ligand with the metal coordinated to the atoms O and N.
In another aspect, Met is selected from Ir and Pt.
In another aspect, (Y)103-Y104) Are carbene ligands.
Examples of the organic compound used as a host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; from the group of aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazines, oxadiazines, indoles, benzimidazoles, indazoles, indoxazines, benzoxazoles, benzisoxazoles, benzothiazoles, quinolines, isoquinolines, cinnolines, quinazolines, quinoxalines, naphthyridines, phthalazines, pteridines, dibenzopyrans, acridines, phenazines, phenothiazines, phenoxazines, benzofuropyridines, furobipyridines, benzothienopyridines, thienobipyridines, benzoselenenopyridines, and selenophenodipyridines; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Wherein each group is further substituted with a substituent selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, the host compound contains in the molecule at least one of the following groups:
R101to R107Independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, carboxyl,isonitrile groups, thio groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, when aryl or heteroaryl groups, have similar definitions as those for Ar described above.
k is an integer from 1 to 20; k' "is an integer of 0 to 20.
X101To X108Selected from C (including CH) or N.
Z101And Z102Selected from NR101O or S.
HBL：
Hole Blocking Layers (HBLs) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a barrier layer in the device may result in substantially higher efficiency compared to a similar device lacking the barrier layer. Furthermore, the blocking layer can be used to limit the emission to a desired area of the OLED.
In one aspect, the compounds used in the HBL contain the same molecule or the same functional group used as the host described above.
In another aspect, the compound used in HBL contains in the molecule at least one of the following groups:
k is an integer from 1 to 20; l is101Is another ligand, and k' is an integer of 1 to 3.
ETL：
The Electron Transport Layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complex or organic compound may be used as long as it is typically used to transport electrons.
In one aspect, the compound used in the ETL contains in the molecule at least one of the following groups:
R101selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, which when aryl or heteroaryl has a similar definition to Ar above.
Ar1To Ar3Have similar definitions as Ar described above.
k is an integer of 1 to 20.
X101To X108Selected from C (including CH) or N.
In another aspect, the metal complex used in the ETL contains (but is not limited to) the general formula:
(O-N) or (N-N) is a bidentate ligand having a metal coordinated to atom O, N or N, N; l is101Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.
In any of the above compounds used in each layer of an OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically listed substituent (such as, but not limited to, methyl, phenyl, pyridyl, etc.) encompasses non-deuterated, partially deuterated, and fully deuterated forms thereof. Similarly, substituent classes (such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc.) also encompass non-deuterated, partially deuterated, and fully deuterated forms thereof.
Many hole injection materials, hole transport materials, host materials, dopant materials, exciton/hole blocking layer materials, electron transport materials, and electron injection materials can be used in OLEDs in addition to and/or in combination with the materials disclosed herein. Non-limiting examples of materials that can be used in OLEDs in combination with the materials disclosed herein are listed in table 1 below. Table 1 lists non-limiting classes of materials, non-limiting examples of compounds of each class, and references disclosing the materials.
TABLE 1
Experiment of
The chemical abbreviations used throughout this document are as follows: SPhos is dicyclohexyl (2',6' -dimethoxy- [1,1' -biphenyl)]-2-yl) phosphine, Pd2(dba)3Is tris (dibenzylideneacetone) dipalladium (0) and tert-BuONa is sodium tert-butoxide.
Example 1
Synthesis of Compound 5
Synthesis of 2-bromo-9- (3- (triphenylen-2-yl) phenyl) -9H-carbazole
2- (3-iodophenyl) triphenylene (7.80g, 18.13mmol), 2-bromo-9H-carbazole (4.46g, 18.13mmol), CuI (0.52g, 2.72mmol), cyclohexane-1, 2-diamine (0.62g, 5.44mmol) and K3PO4A solution of (7.69g, 36.3mmol) in o-xylene (400ml) was refluxed for 4 days. The reaction mixture was filtered through a short plug of celite and the solvent was evaporated. The residue was purified by column chromatography on silica gel with heptane/toluene (9/1 to 7/3, v/v) as eluent to give 2-bromo-9- (3- (triphenylen-2-yl) phenyl) -9H-carbazole (3.3g, 33.2%) as a white solid.
Synthesis of Compound 5
9H-carbazole (1.61g, 9.63mmol), 2-bromo-9- (3- (triphenylen-2-yl) phenyl) -9H-carbazole (4.80g, 8.75mmol), Pd2(dba)3A solution of (0.24g, 0.26mmol), SPhos (0.43g, 1.05mmol) and tert-BuONa (1.85g, 19.25mmol) in xylene (230ml) was refluxed for 20 h. The hot reaction mixture was filtered through a short plug of celite, andand the solvent was evaporated. The residue was purified by column chromatography on silica gel with heptane/dichloromethane (7/3 to 3/7, v/v) as eluent to give compound 5(4.03g, 73%) as a white solid.
Example 2
Synthesis of Compound 6
Synthesis of Compound 6
9H-2,9' -dicarbazole (2.40g, 7.22mmol), 2- (4-chlorophenyl) triphenylene (2.69g, 7.94mmol), and Pd2(dba)3A solution of (0.26g, 0.29mmol), SPhos (0.24g, 0.58mmol) and tert-Buona (2.08g, 21.66mmol) in xylene (15ml) was refluxed for 20 h. The hot reaction solution was filtered through a short plug of silica gel. The filtrate was diluted with heptane and filtered again through a short plug of silica gel eluting with heptane/toluene (1/1). After evaporation of the solvent, the crude product was recrystallized from toluene to yield compound 6 as white crystals (2.90g, 63%).
Example 3
Synthesis of Compound 32
Synthesis of Compound 32
Mixing 9H-2,9' -dicarbazole (2.40g, 7.22mmol) and 4- (3' -bromo- [1,1' -biphenyl)]-3-yl) dibenzo [ b, d]Thiophene (3.00g, 7.22mmol), Pd2(dba)3A solution of (0.27g, 0.29mmol), SPhos (0.24g, 0.58mmol) and tert-Buona (2.08g, 21.67mmol) in xylene (120ml) was refluxed for 20 h. After cooling to room temperature, the solid was removed by filtration. The filtrate was diluted with toluene and filtered through a short plug of silica gel. After evaporation of the solvent, the crude product was recrystallized from toluene to yield compound 32 as a white solid (3.6g, 75%).
Example of computing
Compounds were subjected to computational studies using Gaussian G09, revision C.01 under the B3LYP/6-31G (d) function and basis set to assess the energy levels of selected compounds. The results of the HOMO/LUMO and triplet (T1) energy levels for compound 5 and CC-1 are presented in Table 2.
TABLE 2
Compound 5 has a much higher LUMO level (-1.39eV versus-2.07 eV) than the comparative compound CC-1. The compound CC-1 having such a low LUMO level mainly serves as an electron transporting host, whereas the present compound may have more balanced charge transporting properties. Furthermore, T1 for compound 5 was greater than CC-1(2.76eV versus 2.65 eV). A high triplet host is beneficial to effectively confine triplet excitons to the emitter, resulting in high efficiency electroluminescence.
Example of the device
All devices were passed through a high vacuum (about 10)-7Torr) thermal evaporation. The anode electrode was 120nm Indium Tin Oxide (ITO). The cathode electrode consisted of 1nm LiF followed by 100nm aluminum. After fabrication, all devices were immediately encapsulated in a nitrogen glove box with epoxy-sealed glass lids ((R))<1ppm of H2O and O2) And incorporating a moisture getter into the package interior.
All device examples have an organic stack consisting of, in order from the ITO surface: compound a at 10nm as Hole Injection Layer (HIL), 4' -bis [ N- (1-naphthyl) -N-phenylamino-biphenyl (NPD) at 30nm as Hole Transport Layer (HTL), and the host of the invention (compound 5 and compound 32) or the comparative hosts (CC-2 and CC-3) doped with 15% by weight of compound a at 30nm as emission layer (EML). On top of the EML, 5nm of compound BL was deposited as a Hole Blocking Layer (HBL), followed by 45nm of tris (8-hydroxyquinolinyl) aluminum (Alq)3) As an Electron Transport Layer (ETL).
The chemical structure of the compounds used in the device is as follows:
table 3 provides an overview of the relative device data recorded at 1000 nits: emission color and External Quantum Efficiency (EQE).
Table 3.
All devices emit a green color. As shown in Table 3, devices 1 and 2 using inventive compounds 5 and 32, respectively, as host materials exhibited improved efficiencies compared to devices C-2 and C-3 using comparative compounds as hosts. This enhanced device performance may be attributable to the balance of electron/hole flux due to the improvement in the unique chemical structure of the compounds of the present invention.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. The invention as claimed may thus include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (20)
1. A compound having the formula I,
wherein G is1Having the formula II:
wherein G is2Having formula III:
wherein L is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
wherein G is3Selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
wherein R is2、R4、R6And R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
wherein R is1、R3、R5And R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
wherein R is1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
wherein L is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
wherein G is3Optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, aryloxy, arylthioA group, an arylseleno group, a heteroaralkyl group, a heteroaryloxy group, a heteroarylthio group, a nitrile, an isonitrile, and combinations thereof;
wherein a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
Wherein m is greater than n.
2. The compound of claim 1, wherein R1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBIs hydrogen.
3. The compound of claim 1, wherein the compound is selected from the group consisting of: formula IV:
and formula V:
4. the compound of claim 1, wherein G1The method comprises the following steps:
5. the compound of claim 1, wherein G1Selected from the group consisting of:
6. the compound of claim 1, wherein L is selected from the group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl;
wherein each is independently represented by the formula1、G2Or G3And one of them- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -1A direct bond of (2).
7. The compound of claim 1, wherein G2The method comprises the following steps:
8. the compound of claim 1, wherein G2Selected from the group consisting of:
9. the compound of claim 1, wherein G3Selected from the group consisting of:
wherein X is selected from the group consisting of: o, S and Se, and
wherein R is9And R10Independently selected from the group consisting of: alkyl, cycloalkyl and aryl.
10. The compound of claim 1, wherein the compound is selected from the group consisting of:
11. the compound of claim 1, wherein m is 1, L is benzene, and R is3、R4And RAIs hydrogen.
12. The compound of claim 1, wherein m is 1, L is biphenyl, and R is3、R4And RAIs hydrogen.
13. A device, comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode comprising a compound having formula I:
wherein G is1Having the formula II:
wherein G is2Having formula III:
wherein L is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
wherein G is3Selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
wherein R is2、R4、R6And R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
wherein R is1、R3、R5And R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
wherein R is1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
wherein L is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
wherein G is3Optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
wherein a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
Wherein m is greater than n.
14. The device of claim 13, wherein the organic layer is an emissive layer and the compound of formula I is a host.
15. The device of claim 13, wherein the organic layer further comprises a phosphorescent emissive dopant.
16. The device of claim 13, wherein the phosphorescent emissive dopant is a transition metal complex having at least one ligand or a portion of the ligand when the ligand is bidentate or higher, the ligand selected from the group consisting of:
wherein R isa、Rb、RcAnd RdMay represent a mono-, di-, tri-or tetra-substituent or no substituent; and is
Wherein R isa、Rb、RcAnd RdIndependently selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein Ra、Rb、RcAnd RdTwo adjacent substituents in (a) are optionally linked to form a fused ring or to form a multidentate ligand.
17. The device of claim 13, wherein the organic layer is a barrier layer and the compound is a barrier material in the organic layer.
18. The device of claim 13, wherein the device is an organic light emitting device.
19. The device of claim 13, wherein the device comprises a compound selected from the group consisting of:
20. a formulation comprising a compound having formula I:
wherein G is1Having the formula II:
wherein G is2Having formula III:
wherein L is selected from the group consisting of: benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
wherein G is3Selected from the group consisting of: benzene, furan, thiophene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenophenocarbazole, benzofluorenochiophene, indolocarbazole, and benzothienodibenzothiophene;
wherein R is2、R4、R6And R8Each independently represents a mono-substituent, a di-substituent, a tri-substituent or no substituent;
wherein R is1、R3、R5And R7Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;
wherein R is1、R2、R3、R4、R5、R6、R7、R8、RAAnd RBEach independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, silyl, carbonyl, alkoxy, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
wherein L is optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
wherein G is3Optionally further substituted with one or more substituents selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, aralkyl, aryloxy, arylthio, arylseleno, heteroaralkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
wherein a is 0 or 1; b is 0, 1,2 or 3; m is an integer of 1 to 10; n is an integer from 0 to 9; and is
Wherein m is greater than n.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104926805B (en) * | 2014-03-18 | 2019-10-18 | 环球展览公司 | Electroluminescent organic material and device |
| JP2016056169A (en) * | 2014-09-05 | 2016-04-21 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting element, light-emitting device, electronic device, and luminaire |
| US11447496B2 (en) | 2016-11-23 | 2022-09-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Nitrogen-containing fused heterocyclic ring compound and application thereof |
| CN106611823B (en) * | 2017-01-19 | 2018-07-10 | 江西冠能光电材料有限公司 | A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application |
| KR102407540B1 (en) * | 2017-12-01 | 2022-06-10 | 엘지디스플레이 주식회사 | Organic compounds, organic light emitting diode and orgnic light emitting display device including the compounds |
| EP3674290A3 (en) * | 2018-12-28 | 2020-09-30 | Samsung Electronics Co., Ltd. | Heterocyclic compound, composition including the same, and organic light-emitting device including the heterocyclic compound |
| US20200343457A1 (en) * | 2019-04-29 | 2020-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20220008985A (en) * | 2020-07-14 | 2022-01-24 | 삼성디스플레이 주식회사 | Organic electroluminescent element and polycyclic compound for organic electroluminescent element |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101258221A (en) * | 2005-09-08 | 2008-09-03 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| WO2009021126A2 (en) * | 2007-08-08 | 2009-02-12 | Universal Display Corporation | Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group |
| WO2011111589A1 (en) * | 2010-03-08 | 2011-09-15 | Fujifilm Corporation | Photoelectric conversion device and imaging device |
| JP2012049518A (en) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, compound, organic electroluminescent element, display device, and luminaire |
| KR20120116272A (en) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| KR20120116282A (en) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
| KR20130004780A (en) * | 2011-07-04 | 2013-01-14 | 엘지디스플레이 주식회사 | Blue phophorescene compounds and organic light emitting diode devices using the same |
| CN103155195A (en) * | 2010-10-08 | 2013-06-12 | 通用显示公司 | Novel 3, 9-Linked Oliogocarbazole-Based Hosts, Containing DBT and DBF Fragments, Separated by Aromatic Spacers |
| CN103159745A (en) * | 2011-12-16 | 2013-06-19 | 昱镭光电科技股份有限公司 | Compound used on organic electroluminescent device and organic electroluminescent device |
| KR20130077471A (en) * | 2011-12-29 | 2013-07-09 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
| CN103262283A (en) * | 2010-12-09 | 2013-08-21 | 新日铁住金化学株式会社 | Organic electroluminescent element |
| WO2013165192A1 (en) * | 2012-05-02 | 2013-11-07 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| US20130320837A1 (en) * | 2012-05-30 | 2013-12-05 | Universal Display Corporation | Four Component Phosphorescent OLED For Cool White Lighting Application |
| CN103502243A (en) * | 2011-03-08 | 2014-01-08 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Family Cites Families (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
| DE69412567T2 (en) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co Ltd | Amine compound and electroluminescent device containing it |
| US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
| US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
| US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
| US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
| US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
| US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
| US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
| US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
| US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
| US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
| US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
| US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
| KR100377321B1 (en) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | Electronic device comprising organic compound having p-type semiconducting characteristics |
| US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| JP2002050860A (en) | 2000-08-04 | 2002-02-15 | Toray Eng Co Ltd | Method and device for mounting |
| US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
| JP3812730B2 (en) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | Transition metal complex and light emitting device |
| JP4307000B2 (en) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | Metal coordination compound, electroluminescent element and display device |
| JP4310077B2 (en) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | Metal coordination compound and organic light emitting device |
| DE60232415D1 (en) | 2001-06-20 | 2009-07-02 | Showa Denko Kk | LIGHT-EMITTING MATERIAL AND ORGANIC LUMINAIRE DIODE |
| US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
| US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
| US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
| US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
| KR100691543B1 (en) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | New material for transporting electron and organic electroluminescent display using the same |
| US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
| US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
| EP2264122A3 (en) | 2002-08-27 | 2011-05-11 | Fujifilm Corporation | Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays |
| US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
| JP4365199B2 (en) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4365196B2 (en) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | Organic electroluminescence device |
| EP1606296B1 (en) | 2003-03-24 | 2009-08-05 | University Of Southern California | PHENYL-PYRAZOLE COMPLEXES OF Ir |
| US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
| EP1717291A3 (en) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
| US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
| US20060186791A1 (en) | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
| JP2005011610A (en) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | Organic electroluminescent element |
| US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
| TWI390006B (en) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
| DE10338550A1 (en) | 2003-08-19 | 2005-03-31 | Basf Ag | Transition metal complexes with carbene ligands as emitters for organic light-emitting diodes (OLEDs) |
| US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
| JP4822687B2 (en) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | Organic electroluminescence device |
| US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
| KR100963457B1 (en) | 2004-03-11 | 2010-06-17 | 미쓰비시 가가꾸 가부시키가이샤 | Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same, and method for manufacturing organic electroluminescent device and method for producing charge-transporting film |
| TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
| JP4869565B2 (en) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | Organic electroluminescence device |
| US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
| US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
| US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
| US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
| WO2005123873A1 (en) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | Organic electroluminescent device material, organic electroluminescent device, display and illuminating device |
| CA2568667A1 (en) | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
| EP2178348B1 (en) | 2004-07-23 | 2012-11-21 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
| DE102004057072A1 (en) | 2004-11-25 | 2006-06-01 | Basf Ag | Use of Transition Metal Carbene Complexes in Organic Light Emitting Diodes (OLEDs) |
| EP1859656B1 (en) | 2004-12-30 | 2013-07-17 | E.I. Du Pont De Nemours And Company | Organometallic complexes |
| US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
| KR100803125B1 (en) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | Red phosphorescent compounds and organic electroluminescence devices using the same |
| JP5125502B2 (en) | 2005-03-16 | 2013-01-23 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element material, organic electroluminescence element |
| DE102005014284A1 (en) | 2005-03-24 | 2006-09-28 | Basf Ag | Use of compounds containing aromatic or heteroaromatic rings containing groups via carbonyl groups as matrix materials in organic light-emitting diodes |
| WO2006103874A1 (en) | 2005-03-29 | 2006-10-05 | Konica Minolta Holdings, Inc. | Organic electroluminescent device material, organic electroluminescent device, display and illuminating device |
| US8231983B2 (en) | 2005-04-18 | 2012-07-31 | Konica Minolta Holdings Inc. | Organic electroluminescent device, display and illuminating device |
| US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
| US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
| US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| JP4533796B2 (en) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | Organic electroluminescence device |
| US8092924B2 (en) | 2005-05-31 | 2012-01-10 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
| KR101010846B1 (en) | 2005-06-07 | 2011-01-25 | 신닛테츠가가쿠 가부시키가이샤 | Organic metal complex and organic electroluminescent device using same |
| WO2007002683A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
| JP5076891B2 (en) | 2005-07-01 | 2012-11-21 | コニカミノルタホールディングス株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
| WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
| JP4887731B2 (en) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element, display device and lighting device |
| CN102633820B (en) | 2005-12-01 | 2015-01-21 | 新日铁住金化学株式会社 | Compound for organic electroluminescent element and organic electroluminescent element |
| KR20080085000A (en) | 2005-12-01 | 2008-09-22 | 신닛테츠가가쿠 가부시키가이샤 | Organic electroluminescent device |
| EP2399922B1 (en) | 2006-02-10 | 2019-06-26 | Universal Display Corporation | Metal complexes of cyclometallated imidazo(1,2-f) phenanthridine and diimidazo(1,2-A;1',2'-C)quinazoline ligands and isoelectronic and benzannulated analogs therof |
| JP4823730B2 (en) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | Luminescent layer compound and organic electroluminescent device |
| EP2639231B1 (en) | 2006-04-26 | 2019-02-06 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
| EP2018090A4 (en) | 2006-05-11 | 2010-12-01 | Idemitsu Kosan Co | Organic electroluminescent device |
| WO2007142083A1 (en) | 2006-06-02 | 2007-12-13 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element using the material |
| CN101506192A (en) | 2006-08-23 | 2009-08-12 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element using same |
| JP5589251B2 (en) | 2006-09-21 | 2014-09-17 | コニカミノルタ株式会社 | Organic electroluminescence element material |
| JP4388590B2 (en) | 2006-11-09 | 2009-12-24 | 新日鐵化学株式会社 | Compound for organic electroluminescence device and organic electroluminescence device |
| EP2518045A1 (en) | 2006-11-24 | 2012-10-31 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element using the same |
| US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
| US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
| WO2008101842A1 (en) | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
| DE502008002309D1 (en) | 2007-04-26 | 2011-02-24 | Basf Se | SILANE CONTAINS PHENOTHIAZIN S-OXIDE OR PHENOTHIAZIN-S, S-DIOXIDE GROUPS AND THEIR USE IN OLEDS |
| WO2008156879A1 (en) | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
| WO2009000673A2 (en) | 2007-06-22 | 2008-12-31 | Basf Se | Light emitting cu(i) complexes |
| JP5675349B2 (en) | 2007-07-05 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Carbene transition metal complex luminophore and at least one selected from disilylcarbazole, disilyldibenzofuran, disilyldibenzothiophene, disilyldibenzophosphole, disilyldibenzothiophene S-oxide and disilyldibenzothiophene S, S-dioxide Light-emitting diodes containing two compounds |
| US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| TW200911730A (en) | 2007-07-07 | 2009-03-16 | Idemitsu Kosan Co | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
| US8221907B2 (en) | 2007-07-07 | 2012-07-17 | Idemitsu Kosan Co., Ltd. | Chrysene derivative and organic electroluminescent device using the same |
| TW200909560A (en) | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Organic electroluminescence device and material for organic electroluminescence devcie |
| US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| EP2166584B1 (en) | 2007-07-10 | 2016-06-08 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element prepared by using the material |
| US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
| CN101688052A (en) | 2007-07-27 | 2010-03-31 | E.I.内穆尔杜邦公司 | The aqueous dispersion that comprises the conductive polymers of inorganic nanoparticles |
| JP2009040728A (en) | 2007-08-09 | 2009-02-26 | Canon Inc | Organometallic complex and organic light-emitting element using the same |
| CN101896494B (en) | 2007-10-17 | 2015-04-08 | 巴斯夫欧洲公司 | Transition metal complexes having bridged carbene ligands and the use thereof in OLEDs |
| US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
| US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
| DE102007053771A1 (en) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organic electroluminescent devices |
| JPWO2009063833A1 (en) | 2007-11-15 | 2011-03-31 | 出光興産株式会社 | Benzochrysene derivative and organic electroluminescence device using the same |
| CN101868868A (en) | 2007-11-22 | 2010-10-20 | 出光兴产株式会社 | Organic el element |
| EP2221897A4 (en) | 2007-11-22 | 2012-08-08 | Idemitsu Kosan Co | Organic el element and solution containing organic el material |
| US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
| CN105859792A (en) | 2008-02-12 | 2016-08-17 | 巴斯夫欧洲公司 | Electroluminescent metal complexes with dibenzo[f,h]quinoxalines |
| KR101920513B1 (en) * | 2011-04-05 | 2018-11-20 | 메르크 파텐트 게엠베하 | Organic electroluminescent device |
| CN104271701A (en) | 2012-04-25 | 2015-01-07 | 国立大学法人九州大学 | Light-emitting material and organic light-emitting element |
| KR101576562B1 (en) * | 2013-07-19 | 2015-12-10 | 주식회사 두산 | Organic lightingemitting compound and organic electroluminescent device using the same |
| KR101547065B1 (en) * | 2013-07-29 | 2015-08-25 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20160039625A (en) * | 2013-08-09 | 2016-04-11 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescence composition, material for organic electroluminescence element, solution of material for organic electroluminescence element, and organic electroluminescence element |
-
2014
- 2014-02-21 US US14/186,732 patent/US10707423B2/en active Active
-
2015
- 2015-01-14 KR KR1020150006829A patent/KR102283995B1/en active IP Right Grant
- 2015-02-13 CN CN201510078722.3A patent/CN104860868A/en active Pending
- 2015-02-13 CN CN202011376587.8A patent/CN112390740A/en active Pending
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101258221A (en) * | 2005-09-08 | 2008-09-03 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| WO2009021126A2 (en) * | 2007-08-08 | 2009-02-12 | Universal Display Corporation | Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group |
| WO2011111589A1 (en) * | 2010-03-08 | 2011-09-15 | Fujifilm Corporation | Photoelectric conversion device and imaging device |
| JP2011187663A (en) * | 2010-03-08 | 2011-09-22 | Fujifilm Corp | Photoelectric conversion element and image pickup element |
| JP2012049518A (en) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, compound, organic electroluminescent element, display device, and luminaire |
| CN103155195A (en) * | 2010-10-08 | 2013-06-12 | 通用显示公司 | Novel 3, 9-Linked Oliogocarbazole-Based Hosts, Containing DBT and DBF Fragments, Separated by Aromatic Spacers |
| CN103262283A (en) * | 2010-12-09 | 2013-08-21 | 新日铁住金化学株式会社 | Organic electroluminescent element |
| CN103502243A (en) * | 2011-03-08 | 2014-01-08 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR20120116282A (en) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
| KR20120116272A (en) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| KR20130004780A (en) * | 2011-07-04 | 2013-01-14 | 엘지디스플레이 주식회사 | Blue phophorescene compounds and organic light emitting diode devices using the same |
| CN103159745A (en) * | 2011-12-16 | 2013-06-19 | 昱镭光电科技股份有限公司 | Compound used on organic electroluminescent device and organic electroluminescent device |
| KR20130077471A (en) * | 2011-12-29 | 2013-07-09 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
| WO2013165192A1 (en) * | 2012-05-02 | 2013-11-07 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| US20130320837A1 (en) * | 2012-05-30 | 2013-12-05 | Universal Display Corporation | Four Component Phosphorescent OLED For Cool White Lighting Application |
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| Publication number | Publication date |
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| KR102283995B1 (en) | 2021-07-30 |
| US10707423B2 (en) | 2020-07-07 |
| US20150243894A1 (en) | 2015-08-27 |
| CN104860868A (en) | 2015-08-26 |
| KR20150099395A (en) | 2015-08-31 |
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